Reaktion #634120

Reaktionsgleichung

(2,4-Dichloro-phenyl)acetic acid methyl ester

2-dicyclohexylphosphino-2′,6′-dimethoxy-1,1′-biphenyl

potassium phosphate

(E)-4-(4-{1-ethyl-1-[3-methyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-propyl}-2-methyl-phenyl)-1,1,1-trifluoro-2-trifluoromethyl-3-buten-2-ol

→

compound

Ausbeute 7.1%

(3-chloro-4′-{1-ethyl-1-[3-methyl-4-((E)-4,4,4-trifluoro-3-hydroxy-3-trifluoromethyl-1-butenyl)-phenyl]-propyl}-2′-methyl-biphenyl-4-yl)-acetic Acid Methyl Ester

Ausbeute 7.1%

Lösungsmittel

toluene

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   FiltrationThen, the reaction mixture was filtered through amino silica gel
2. 2
   Einengenthe filtrate was concentrated under reduced pressure
3. 3
   SonstigeThe resulting residue was purified by silica gel chromatography (hexane:ethyl acetate=2:1)

Vorschrift

(2,4-Dichloro-phenyl)acetic acid methyl ester (Example 41; 28.7 mg, 0.131 mmol), palladium acetate (2.0 mg, 0.009 mmol), 2-dicyclohexylphosphino-2′,6′-dimethoxy-1,1′-biphenyl (7.2 mg, 0.018 mmol), potassium phosphate (56 mg, 0.263 mmol) and water (0.1 mL) were added to a solution of (E)-4-(4-{1-ethyl-1-[3-methyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-propyl}-2-methyl-phenyl)-1,1,1-trifluoro-2-trifluoromethyl-3-buten-2-ol (Example 26-(5); 50 mg, 0.088 mmol) in toluene (1 mL). After replacement with nitrogen, the mixture was stirred at 100° C. overnight. Then, the reaction mixture was filtered through amino silica gel, and the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel chromatography (hexane:ethyl acetate=2:1) to give the target compound as a colorless oil (3.9 mg, 7%).

Quelle